HCID 10179280, compound → HCID 69364625, compound

HRID 723752Notes

Reaction equation

HRID 723752 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][N:23]5[CH:27]=[CH:26][N:25]=[N:24]5)[O:19][C:18]4=[O:28])=[CH:13][C:12]=3[F:29])[CH2:7][CH2:6]2)[O:4]CC1>C(O)(=O)C.O>[O:4]=[C:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][C@H:20]([CH2:22][N:23]4[CH:27]=[CH:26][N:25]=[N:24]4)[O:19][C:18]3=[O:28])=[CH:13][C:12]=2[F:29])[CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 10179280HCID 10179280, compound

Product 1

HCID 69364625HCID 69364625, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

(5R)-3-(4-(1,4-Dioxa-8-azaspiro[4,5]dec-8-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one (1.47 g, 3.65 mM) was dissolved in a mixture of glacial acetic acid (30 ml) and water (30 ml), and heated at 50° for 18 hours. Solvent was evaporated, the residue azeotroped with toluene (50 ml), then partitioned between ethyl acetate (150 ml) and water (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution (2×100 ml), water (100 ml), dried (magnesium sulfate) and evaporated to give product (894 mg), of sufficient quality for use without purification.

Workup

  1. temperatureheated at 50° for 18 hours
  2. customSolvent was evaporated
  3. customthe residue azeotroped with toluene (50 ml)
  4. custompartitioned between ethyl acetate (150 ml) and water (100 ml)
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (2×100 ml), water (100 ml)
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated

Sources & evidence

ORD record
ord-f0d2977a3e064760beae2aa8b8e255c3
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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